Rearrangement of 4-imino-(1H,4H)-3,1-benzoxazine-2-ones to 2,4- quinazolinediones via an isocyanate carboxamide intermediate

Tetrahedron Letters

Volumn 41, Issue 27, 2000, Pages 5265-5268

  Azizian, Javad ^a   Mehrdad, Morteza ^a   Jadidi, Khosrow ^a   Sarrafi, Yaghob ^a  

^a SHAHID BEHESHTI UNIVERSITY   (Iran)

Author keywords

Benzoxazines; Carbamates; Quinazolinones; Rearrangements

Indexed keywords

AMIDE; BENZOXAZINE DERIVATIVE; CARBAMIC ACID DERIVATIVE; ISOCYANIC ACID DERIVATIVE; QUINAZOLINE DERIVATIVE;

ARTICLE; CARBON NUCLEAR MAGNETIC RESONANCE; CHEMICAL ANALYSIS; CHEMICAL REACTION; OXIDATION; REACTION ANALYSIS; SYNTHESIS;

EID: 0034235217     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(00)00803-0     Document Type: Article

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29. 13C NMR (125 MHz, DMSO) δ (ppm): 162.2 (C-4), 150.1 (C-2), 139.8 (C-8a), 135.7 (C-1′), 135.1 (C-7), 129.0 (C-2′, 6′), 128.7 (C-3′, 5′), 128.0 (C-4′), 127.5 (C-5), 122.4 (C-6), 115.2 (C-8), 114.3 (C-4a).
30. 13C NMR (125 MHz, DMSO) δ (ppm): 167.1 (C-amide), 153.5 (C-carbamate), 138.6 (C-2), 138.5 (C-1′), 132.1 (C-5), 128.8 (C-3), 128.5 (C-3′, 5′), 124.1 (C-4′), 122.2 (C-4), 122.2 (C-1), 120.9 (C-2′, 6′), 119.7 (C-6), 52.0 (C-methyl).
31. 13C NMR (125 MHz, DMSO) δ (ppm): 146.8 (C-2), 145.1 (C-4), 142.0 (C-8a), 139.6 (C-4′), 134.0 (C-7), 133.2 (C-1′), 129 (C-3′, 5′), 126.9 (C-5), 123.5 (C-6), 122.4 (C-2′, 6′), 114.4 (C-8), 114.1 (C-4a).